I Knew You Were Trouble
by salvatoredarlingx
Summary: In the wake of Elena's brand new album release, her life seems to be perfect. Some people even call her one of the lucky ones. But she didn't feel lucky, at least sometimes she didn't. But when her manager suddenly drops her, she must find a new one. And the best candidate is bad boy, Damon Salvatore—who has a few secrets. A/U
1. 1: It Is What It is

**Ah, hello all! Brand new story. It's been in the works for a whilee. This isn't edited much, but I wanted to release it for a tease. I'm really excited to get busy on it. Thank you again for everyone's extremely kind words for Hostile Takeover. It pretty much makes me smile everytime I see someone new or a comment. I hope you all love this fanfic. I personally do, if you haven't figured out, it's based on Taylor Swift's song & music video, "I knew you were trouble." It's Alternative Universe, but Damon does have some lovely secrets. ;) Thank you again guys! xo**

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Preface:

_I guess it's the fact I lost myself. I lost myself in everything I did, and everything he was. I loved it. He's so much of an angel, with his smile. I was putty in his hands, with every action he did, and every secret he exposed. I was trapped, and I didn't choose to escape his grasp. I didn't feel like I should, or could. I didn't have the will. I knew that was for sure._

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Chapter 1;

"What do you mean he dropped me?" I scream into my silver iPhone, walking around my apartment feeling flustered. On the other line is Caroline Forbes, one of my best friends. I could hear the heavy sigh exiting through her mouth.

"He is going to be Katherine's manager, you know, Katherine and her pushy demands," Caroline reminds me. Katherine Pierce was Billboard's hottest leading lady on the charts, and everyone seems to adore her…at least almost everybody. I roll my eyes flipping through the People magazine that was lying on my coffee table.

"I know," I groan in my most disgusted tone. "That's how it goes, Care. Two weeks before my album release and boom, there goes Stefan with some other client. I don't care, right? Stefan asked for too much in our contract anyway. He was too precise with everything I was doing with my life."

Stefan Jefferson. He's tall and charming, just turned 28 years old. I remembered our friendship as it was yesterday. Stefan was first starting out as a manager, for an indie recording artist, and I was across the hall of the condominiums at Hayden's Peak. He heard me singing one day, and boom that's where our story started. We both gave each other the push we needed to succeed in the cruel entertainment world.

We were a team, and I enjoyed playing on that team. Now, Stefan is playing with the major league of the recording artists, and dropped me when it came to a chance to advance.

Caroline agreed. "It doesn't help you two dated either…" Of course this is exactly why I have Caroline on my side in everything, bringing up my dreaded past, that inspired most of my songs. The sigh in Caroline's voice was depressing. "You know you gotta release another single, people are waiting."

I roll my eyes._ Ugh_. _I'm doing everything by myself._ _Was my album not good enough? Did Stefan ditch me because he had a love for the pop princess?_ I feel like I'm going to barf up my lunch. "I know! Nothing is helping this situation. I should quit now when I'm ahead," I sound like I'm giving up, maybe I am. This is the change of everything. I've always wanted my own album and this is ruining my plans. "Write a song about this too…" I chuckled to myself, as the persistent joke between Caroline and I continued.

"Then really show him a lesson!" Caroline giggled to herself.

"Oh, of course it will."

"So, what are you going to do now?" Caroline questions me with a shrug. You could hear it perfectly, oh, and the nosiness.

"I'm meeting with a new one today," I sigh to myself enough for her to hear my answer.

"Oh really?! And who's that?" she egged on another question.

"His name is Damon… Tyler Lockwood was talking about him one night. He doesn't have clients at the moment, and apparently he's pretty damn good," I explain to my best friend, making myself comfortable on my leather couch.

"…Damon."

"Yes?"

"Damon Salvatore?!" Caroline gasps.

"Uh, I guess, so…" Was I missing something? I think I was.

"You can't work with him, that dick!" She screams as I yank my phone quickly from my ear, and place it on speaker phone, even though that is not needed at the moment. I set it on the table and listened.

"And why is that, Caro? I need this going. I don't care. I need this to work," I was tripping over my words, but I was dying to know what Caroline was yapping about.

"He is a world class dick. Damon has sold so many albums it's fucking insane, and he loves the publicity, and he isn't the best candidate for your problem."

I roll my eyes again. "I'll find out for myself." I finish picking out an outfit to arrive at Salvatore Incorporated. I wasn't too big on finding a new manager, but hell, I needed one. The building wrapped in a silver wall, and glass windows was out of this world. I, myself was shocked. I rolled my eyes again, entering the Valet Parking area, and handing my keys to the young man, who soon took my red '98 Chevy. I walked to the elevator, making sure I was going the right way as I entered. I pressed button 13 as it lit up, and closed the doors.

I escalated through the many floors of the large business building. I felt the goose bumps creep up my arm and my back awaiting my fate.

I waited patiently. This was a first for me. Was I going to have to audition in front of him? Would I be good enough? What did Caroline mean exactly?

Entering the business office, I finally spotted the room down the long hall, which read _Damon Salvatore: Manager of Salvatore Incorporated._

I scrunched my face, and opened the door quietly, viewing the large business office. It was extravagant, and do I mean _extravagant. _This place would blow anyone away. There was a large, mahogany-colored desk, with a receptionist sitting behind it, staring attentively at her computer.

"Hi, I'm here to see Damon Salvatore," I lean barely over the counter as the receptionist glanced up.

"Oh, I see. He'll be through with his meeting in a minute. I'll let you know, Miss-?"

"Gilbert. Sorry. Elena Gilbert," I stuttered falling over my words again. Stefan's aura of plan of action was very much different than this. I had never had to practically beg for someone to be my manager. I have no other choice. That's the song and dance I keep saying to myself.

I find a seat, on the large white cushioned couch, and place my sweaty hands in my lap. My time seemed to tick slowly, so I gaze around admiring the many things plastered on the walls before me. There were plaques, and golden records lining the whole wall. I was flabbergasted by this man.

"Damon Salvatore will see you now."

I snapped out of my daydreams, and removed myself from the couch. I enter his office, and found out quickly of how much he was liked and hated. This was already moving too fast. I sit down, not realizing the man wasn't even present. _Oh, I see how this is going to go. I'm dreading my decision before it even begins._ "What are you doing in my office?" I hear a growl from behind me. My eyes scanned the man quickly up and down. His black leather jacket was an eye catcher. I felt myself gazing at him constantly. His pushed back, black locks were layered, and his smile was perfect. Soon, it turned into a smirk.

"I'm Elena Gilbert, the girl who needed a manager. I'm about to go on tour," I ramble, and then stop in the middle of my sentence watching him slide his hands into his tight jeans' pockets.

He shrugged carelessly, "So you want my assistance? Who did you lose it to, that Taylor Swift girl or Lady Gaga?" He chuckled to himself as I cock my eyebrow with disgust.

_You're not funny, sir._

"Neither, it was Katherine Pierce," I rebutted.

"Ah, Miss Katherine, taking the entertainment world by storm," he roll his eyes, making his way to the leather chair sitting behind the desk, then propping his feet on the desk. _Seems like a fan. NOT._

I stare blankly, then at his worn biker boots. "Isn't she?" I sarcastically threw back at him. I didn't have time for this bullshit. I was in there to make a career out of myself, and I need his help.

"You don't seem too pleased with a rival, Miss Gilbert," he shrugs while stating the obvious.

I could not stand Katherine. She had the media putty in her hands. I was quiet, and he caught on quickly to my silence. _Of course, I didn't!_ Katherine got everything she ever wanted.

"Fine, what do you want from me? You want me to make you into the best recording artist ever? Or do you want the easy version of you getting famous like a snap of a finger?" he snapped his fingers and smirked. His blue eyes were piercing. I didn't like it. One bit.

"I just want to make a name for myself, and get my career going. I can leave if you want, since you are so uninterested."

He laughs.

I stare at him; actually it was more of a harsh glare. I could even feel it. "What are you laughing at?"

"How do you know I am not interested? I love offers. It's what I do."

What have I gotten myself into? He is _not_ manager material. I'm just another client on his long list of singers.

I roll my eyes at him. "Fine."

_That wasn't a very good answer. Shit. Gilbert, you can do far better than that lame comeback._

"Oh calm down, I can see your blood raging at me. I'm harmless, I swear," he smirks again and I sit in disgust. If I was an animal, I would have already ripped his face off. But I could not even do that.

"I do not enjoy being patronized, Mr. Salvatore. I am a human being," I rebutted. I didn't like him, but he might be my only hope. He was strict and to the point, and cynical. I hated everything about him, but at the same time, he seemed to know exactly what he was doing.

My eyes lowered as I planned on giving up. "That's better, put the claws away," he folded his hands on his desk.

"Now, please explain to me what music means to you."

His voice was gentle and tender. I was scared he was going to attack me at any moment. He was too sly for my own good. I was already dissecting everything about him!

"It's a passion of mine, it always has been. I want to get out there, and I can't without a good manager, and my other one dropped me."

"That's what I like to hear," he nodded.

I vision myself begging in front of him on bended knees, completely at his mercy. Tyler Lockwood knew exactly who and what not to deal with, even if this one might be the death of me. "When does your album release?" Damon asked.

"Two weeks from now."

"Do you have a single out?" he questioned. He was very sharp and to the point with his questions, which I kind of liked.

"I have a one playing on radio, and that's it." My stomach dropped. Stefan was so slow on the process of being a manager; I had nothing on the table to offer except a finished record and a single.

"Oh boy, you are going to be some work, I guess I can do it," he commented.

My body tensed up. I smiled unpleasantly, and nodded, "Alright, Mr. Salvatore."

"No, no, please call me Damon, unless you prefer calling me Mr. Salvatore," he whispers coyly. He is completely full of shit. I want to hit him.

"Don't flatter yourself, just because you have a bunch of platinum-selling recording artists under your belt."

He cocked his eyebrow and chuckled with a cynical-tone attached, "Isn't the saying, 'don't bite the hand that feeds you?"

I couldn't help but stare with disbelief of him. He was out there, in his own world, and probably never coming back to earth either.

"So, are you interested in releasing a music video? Or has that never crossed your mind?" he questioned again. He needs to stop opening his big mouth.

I was shocked; he was actually going to try to help me, even though he seemed to not care one bit. "That sounds great. When do we start?"

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**So what did you guys think?! I want to hear about it. Reviews are lovely!**


	2. 2: Know Your Enemy

**Hi guys! I apologize for the long wait for this second chapter. I've been looking forward to updating, especially since I have a LOT mapped out. Firstly, thank you for all the subscribers and comments! I really appreciate it. Thank you to one of my best friends Katy for looking over this for me and helping me out. Couldn't have done this chapter without her! And also, the songs mentioned, Damon is pretty much John Mayer. So, most of his songs are going to be John Mayer ones unless stated otherwise. Thank you again. I hope you enjoy this chapter. ;D**

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Still shocked, I shook my head wondering his motives. He is being_ nice_. Even though I didn't like him, I made sure he knew I was paying attention.

Damon shrugs. "Whenever you have a date available, I'll be here I suppose."

His answer is annoying already. Let's face it, Elena. He might be the push you need. "I'm open. My schedule is very flexible." It was true, the biggest thing I had coming up was Caroline's birthday party.

"Good. I like flexible. It gets things done."

I feel my cheeks blush. The inner little girl in my head is laughing at me. Flexible huh? I bit my bottom lip. "I know. It really does," I agree with him trying to be as professional as possible.

"I like to hear that. I'll call up People Magazine, get you a cover story, or some kind of story. Sound good?" he leans over the table and smirks.

I nod quickly, and slowly lean back as his face is now in mine.

"Here's my card. I'll get in touch with you as soon as a deal is made," he advises to me.

As I left his office, I started to notice how much of a dick Damon was, and how Caroline was completely correct about her feelings toward him.

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"So, how was the conference?" Caroline asked over the phone.

I shrug to myself, "Eh. It could have gone better; he's very to the point…and a dick."

"Not going to tell you I told you so!" she blurts out.

I frown. "I know, I know, but if I can get at least started as a recording artist, I will be okay. I'm worried my plans won't pan out."

Caroline agrees, knowing this has always been a dream of mine, and I wasn't going to let anyone stand in the way of it. "So what's on the agenda?"

I begin to explain to her the big plans he has for me and my music. "Really not sure what's going to happen, hopefully this will work out correctly, and he won't mess up anything."

I can hear the smile on her face, but at the same time, she knows this is a big step for me. This can make or break me.

As I arrive home, I throw my shoulder bag and my keys on the nearby computer table, and make my way to my leather office chair, and fire up my laptop.

It boots up quickly, and I click on Firefox, and load Google. With a click in the search bar, I type in _Damon Salvatore. _My curiosity was getting the best of me right now. Why was everyone so hell bent of making me not like him? After I hit enter, thousands and thousands of searches came up. Some of the results I hated, and some intrigued me. I clicked on the Vevo Youtube page, and discovered he was an artist himself. For once in my life, I was not familiar with an artist.

His music vibe fed off indie rock and classic rock. I was completely captivated by Damon's voice, and the way he dressed especially. I was already becoming a fan of him. My cursor moved over to a few of his tracks including "Stop this Train," "The Heart of Life," and "Gravity." They became my favorites. My mind had become trapped on YouTube which seemed like hours had past.

I bit my bottom lip, trying my damnedest to learn all about him. Damon had accomplished so much in his 28 years, it motivated me to get my shit together and strive for excellence more than ever. His songs were delicate, and could make any girl completely fall to her knees in awe. His writing was a journey it seemed. A journey that stopped abruptly after his break-up with someone, but who was the cause of Damon to stop writing?

My writing is the utmost important thing in my life, and someone took that muse away from Damon. My mind wandered back to Google. "I'm Gonna Find Another You", was the last track Damon had ever unleashed to the world. I clicked on his fansites, seeing how dedicated his fans were. They were extremely dedicated, and one wrong relationship ended that for them.

Then that's when I discovered, Damon's love that hurt him. Katherine Pierce.

I cringed at most of the article. She was a wicked bitch just like I imagined her to be. She was the root of Damon's tragic music end. Besides of using music as a gateway, it harbored his heart. I was struck with the same pain, but my relationship was minor to his. He had been with Katherine for 5 long years and never gave up on her, until she gave up on him. Now she's making hit records because of him, and he's losing, while she's on stage every night singing about him, and making their relationship his fault.

I clicked out of the long article, and rolled my chair away from the computer screen. My cell phone abruptly rang. I ran over to my purse, and dug for it, finding it was Caroline.

"H-Hello?" I asked.

"Something wrong, Lena?" Caroline asks at my stutter.

"N-No, not at all, what's up?" I question changing the subject.

"You're acting funny, but okay. I just thought you might want to get a drink," Caroline asks.

I snap my head out of my iPod, while downloading a few tracks of Damon's album _Continuum. _I realize Caroline is still on the other line, and I perk up and immediately say yes to her request. I need a drink, and after realizing who my boss is, I need a few more than one.

"Cool, I'll come by your house, I'm having boy troubles, and I'll probably need a taxi after this night."

I roll my eyes. Caroline is always an alcohol junkie when her love life is going down the toilet. I sigh. I fix my hair, and put on one of my favorite strapless dresses, and wrap my neck with one of my favorite scarfs.

I wait for Caroline, while continuing to listen to his music. If I had a favorite artist it was beginning to be him. A peck on the door knocked me out of my daydream of Damon. To my escape, it was Caroline.

"So why are we going to a bar again?" I asked her as we walked down the street to the infamous bar _The Timbers. _I wasn't big on bars, but this was different than other dives. I actually hated them, but The Timbers had a certain vibe to it, that made bar-going okay.

"Klaus is a jerk. I can't stand him. This relationship thing sucks!" she mumbles.

Klaus Mikaelson is his name. He's a world class jerk, I have never liked him. Probably never will at this point. He's from England, and he's in a band. Klaus can also make any girl with his suave moves. I prefer to gag. Yuck.

I frown at her ranting. "Break-up again?" I narrow my eyebrows.

Caroline nods. "Things keep going wrong. So terribly wrong, I just want to give up." Poor Caroline never found the right love yet. Relationships were never working out for her, and it made me sad for her. At the same time though, it made me not want one at the moment. "What's your problem that needs some alcohol?"

"I have to release a new single. I don't know which song to pick," I grumble also. "Damon is something. He wants me to release a new single, and he wants to put me on the cover of People Magazine. I just don't really know what to do. It's all happening so fast."

She nods. "Seems like it, but at least he's giving you a chance. I don't think he'll give just anyone a chance."

"Why do you say that?" I ask her opening the door to the bar as we arrive.

Caroline shrugs meeting back up with me walking with me. "He's a jerk. He's always been a jerk. I honestly can't stand him. I don't like him, and his music just makes me hate him more."

I scrunch my face up in disgust of what Caroline was saying. His voice was an angel, and his talent was mind-blowing. "What do you have against him?"

She makes her way to the bar, and plops down ordering herself a mixed drink. Caroline propped herself up with her palm and chuckles, "You'll find out soon enough. You have to learn yourself. Since you are being stubborn, but don't say that I didn't warn you. I have listened to Tyler bicker about Damon. Damon is a dick, and will never change. He got his heartbroken over one stupid girl, and now he makes sure that anyone who comes around him will feel his misery."

"You're right, Caroline, I will learn. I just got dumped by my damn manager because he had the hots for Katherine Pierce. I don't care if he's a dick; all people are dicks in some form. If him being a dick makes it hard for me to be close to him, or have a relationship with him, then so be it. That's probably what killed Stefan in the first place." Why was I suddenly defending him? I breathed out and looked at Caroline. "I just don't want a replay. Being in a relationship with Damon would probably ruin my career. At least not mixing business with pleasure would probably prevent that."

Caroline nods in agreement taking a large swig from her tall glass. "I know, Elena. Be careful though. That's all I'm saying. I don't want you to get hurt this time."

I hug her and let out a sigh, sitting back down on my seat. I order bourbon, and glance over at the spotlight artist. The other good thing about The Timbers is the open mike, and the wonderful indie artists that play there nightly.

But suddenly, the voice coming from the corner was a new voice, and one I had just grown to be attached to. It was Damon. _No it couldn't be Damon_. Damon Salvatore was playing at a bar. This was a treat for me. My inner fangirl was screaming inside.

He was playing a few covers, which fascinated me. I couldn't believe this was my manager. His voice was so relaxing, and somehow made me the happiest person alive. I listened attentively and gazes at his beauty. He dressed to the nines, even if it was jeans and a button down plaid shirt. He wore a fedora to top off, and had his infamous biker boots on.

As much as I tried to shake him, he consumed me in every way possible, because of his incredible talent. I loved anyone who could play music. "Elena, I think I drank too much…" Caroline groaned laying her head down on the bar, as I turned to my best friend who was out of it.

_Sigh._

"Oh dear," I whispered for only myself to hear.

Damon kicked in with her newly downloaded song, "Stop This Train." After he finished his set, I helped Caroline out the door and to a taxi. She was drunk as a skunk.

"Come on, Caroline," I grumbled picking her up, and sitting her down in the cab. "Let's get you home."

I watched Caroline as we rode in the back. She was almost asleep, and I felt the need to pass out at any given moment. The drive was quick and to the point, and before I knew it, I was carrying Caroline to my couch for her to crash.

I placed my iPhone on my iHome, and fell asleep to my newly downloaded songs.

* * *

I woke up the next morning, groggy. And to make my life even better, my phone was ringing repeatedly. "Hello?" I managed to get out to the unknown caller.

"Gilbert, do you realize what time it is?" That velvety voice I fell asleep to was screaming at me, and he wasn't being very nice.

My eyes shot open and I was screaming a long list of curse words in my head. "It's…"

He cleared his throat. "It's noon. Are you planning on getting to the things I sent to you last night?"

I furrowed my eyebrows not knowing for sure what he was talking about. "What things?"

"Oh what, your cell phone doesn't work now or your emails?" _Was he scolding me? Was Damon Salvatore scolding me?! _I was appalled. My mouth dropped open immediately listening to him. _How dare he! _

"I didn't get anything from you! All I got was a call from my friend last night! And my emails, for your information, have been collecting cobwebs for the last 3 months!" I groaned; it was almost a whine.

"Well, you need to get your butt down to my office immediately so we can start your damn appearance dates, and your radio tour!" he yelled.

I moaned to myself. "Fine, I'm on my way!"

"Good!" he hung up after that.

I roll my eyes. I quickly hurry to get dressed, slipping on my left high heel shoe, and tapping for Caroline to get up. "Caroline! I gotta go, Damon called me and he's pissed, I gotta get down to his office. You can stay but I have to get my ass down there before his head explodes!"

Caroline nods and shoos me out the door.

I finally arrived at his office. It was embarrassing almost—the silence. I knock on his office's door. "Come in," he says in a soft tone.

_Well, I'm screwed._

I open the door, and there is Damon in his best attire, staring at me, and may I add I'm extremely uncomfortable at the moment. "Damon." I nod greeting him, but his body language says it all.

"Hello, Miss Gilbert," he hissed.

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**Reviews are lovely ;D**


	3. 3: New York State of Mind

**Yes! I finally get to update, and it's a long one. I really enjoy this fanfic already. Hostile Takeover will be updated soon enough. I apologize for the wait. :) Most of the songs mentioned are by John Mayer, Kate Voegele, and Sara Bareilles. I enjoy reading all the comments also. Thank you so much for all of them. **

**xo Lexi**

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_Hello, Miss Gilbert._

I stare blankly at him. I know he was expecting an explanation, but I just found a seat in front of him and sat down quickly in a leather chair.

"What's on the agenda?" I perk up with a question, trying to make him forget my lack of answering my phone.

He smirks, which I still have no idea what that means. Damon gazes at me and finally speaks. "I need your new single. Did you decide?" he says in a soft, melancholy tone. I was worried by the attitude.

"Y-Yes," I stutter, digging through my purse for the CD with my demo. I locate it, and hand it to him swiftly, expecting the worst from him.

I was confident in this choice. It was one of my favorite songs, and I had written it when Stefan dumped my record deal.

Damon accepts it, and opens the plastic case. He places it in his computer, and allows it load. Suddenly, my piano playing kicks in, and then my voice; and he stares going into a muse.

_Head under water, and they told me to breathe easy for a while  
Breathing gets harder, even I know that  
You made room for me, it's too soon to see, if I'm happy in your hands  
I'm usually hard to hold onto, blank stares at blank pages.  
No easy way to say it. You mean well, but you made this hard on me;_

I'm not gonna write you a love song, 'cause you asked for it, because you need one  
You see, I'm not gonna write you a love song, 'cause you tell me it's make or breaking this  
If you are on your way, I'm not gonna write you to stay.  
If all you have is leaving. I'mma need a better reason to write you a love song  
Today.

I sigh, as I got through the first verse and the chorus without him flipping it off or saying something harsh. "What's it about?" he asks bluntly. "I know what it's probably about, but I want to hear it directly from the artist."

"I felt like I was expected to outdo Katherine, because I didn't want to lose my record deal, but it slipped through my fingers quickly. And Stefan and I already have a past, so…" I trailed off with a sigh.

He nods—perhaps in agreement? Katherine did break his heart, and he probably knows that pain. "That's what I thought."

Is this approval? I'm shocked.

"So you got over it, and you aren't going to beg him to stay."

I bit my bottom lip and slowly nodded my head. He knew me already.

"Well, I like it. It's one of those catchy songs, that will be everyone's favorite song, and will be blasting it on the radio," he finally stated.

"Thank you," I answered simply. I wasn't sure what else to say. First song and he already likes it. How many more songs has he heard by me? It concerns me of his opinion. I care about his opinion of me. _That's treacherous just thinking that._

He nods, and continues his paperwork. "You have a radio tour coming up. It's the best way to get out there, plus with your song on the radio, people will be dying to hear you." His advice was good, more than good. It was what I needed. He was giving me that start, and it was already moving too fast.

I breathe in. "Sounds good. When?"

"Starts next week, in New York of course. You probably have a well-balanced fanbase here, am I correct?" he mutters with a curious motive.

I nod quickly in total agreement of Damon's choice of starting my radio tour. He has the dates listed on a piece of white paper, written in his handwriting. "You are allowed to do covers, also, if you like," he continues.

I sigh. I had a few in mind. I lift my head up and stare at him. I was quiet, and he knew it.

"I'll leave that to you, Gilbert," he gestures.

So the next few days, I spent my time writing out my songs I wanted to sing.

My singles of course: "Love Song" and "Angel;" I would have to play. Off my album, "Bottle it Up," "Many the Miles," and "Gravity." I ponder for a moment about the covers that I want to do. There were plenty as I search through my iPod. _The Heart of Life appears. _One of my favorites by Damon; I turn my headphones up, and listen to his voice, as I harmonize with his.

I search through the long lists of artists, and find Taylor Swift. "Mine" was always one of my favorites. The final song I chose was "Ordinary Day," by Vanessa Carlton. That was just for my first concert. _Phew_.

Maybe this could go well. Damon seems to think so.

Day 1: New York City.

I wake up with full intentions and anxiety trying its best to settle in. I literally jumped out of bed with excitement. This was it. This is the day I start my radio tour. New York—my home; I was going to sing for them. It's a wonderful feeling.

I finish listening to my playlist, full of my songs, singing along as I go. I look down at the clock, and it's only 1pm. It's going to be a long day.

My phone rings and I know who it has to be—Caroline.

"Hi Caro," I greet her holding the phone with my shoulder.

"Hey Rockstar, are you ready for tonight!?" Caroline screeches. I can hear the pure excitement in her voice.

Oh dear, she's always been a big fan, even when I sucked.

"I guess I am. Are you coming with Klaus?" I question her, taking a bite of my bagel coated with cream cheese.

"Of course! I want to come; you better let me in!" she urges.

I laugh, "You have to be there, Caroline!"

She hangs up shortly after explaining she needs to find the perfect outfit, and tell Klaus about the plans. I'm busy doing the same thing, and debating whether or not I should add a few more songs, just in case.

Time's ticking away, and I'm getting more nervous, I remembered that Damon told me to meet him there early around four to warm-up. My nerves were feeling like fireworks about to set off.

* * *

It was almost four, and The Manhattan Square was deserted. My heart was jumping around; making me fear no one would show. I know my friends were raving at Mystic Grill to come to my performance tonight. I was hoping it would come through.

I make my entrance in the back lot, hearing soft music on the stage. I begin to walk faster through the backstage area, allowing the music to be heard better the closer I got.

I swallowed my fears of what was awaiting me, but there sat Damon Salvatore sitting on a stool playing a guitar. My heart immediately dropped to my feet, making me stop dead in my tracks. My eyes were locked on his guitar, which was grasped by his long fingers, and his frets.

_It's really over, you made your stand.  
You got me crying, as was your plan.  
But when my loneliness is through, I'm gonna find another you.  
You take your sweaters, you take your time  
You might have your reasons, but you will never have my rhymes.  
I'm gonna sing my way away from blue, I'm gonna find another you_

I walk slowly up to him, listening to him perform. He was mesmerizing; I could not take my eyes off of him.

He continues to play, moving his fingers along the neck of the guitar. I creep up, and my cowboy boots' heels gave me away. Damon immediately stops and frowns.

"Yes?" his voice is ice cold.

I sigh, "I was just listening…"

He cocks an eyebrow and smirks. "I see you are a fan?" It's almost a groan of being disgusted.

"I've heard a few," I admit bluntly, playing with the hems of my short dress.

"Wonderful," he mutters in the most sarcastic tone I have ever heard.

I fiddle still, trying to keep my nerves under control, then I hear Damon again.

"What are you laughing at?" I spoke through my teeth at Damon, who was chuckling away at me.

"I'm…nervous."

"You need to chill. It's a small venue; everyone loves you on the radio. You're in the top ten on iTunes," he reminded me frankly.

I bit my lip and nodded. "Okay."

His eyes were subtle and almost caring. "Would you like to warm up?"

I squint my eyes at him, not even meaning to. "S-Sure." My answer was so uneasy. Oops.

"Come on," he motions for us to go backstage.

I follow him.

Damon pulls a seat in front of me, and then pulls another one across. I watch him. "Sit. You got 20 minutes, Gilbert." He sits quickly on the edge of one of the plastic chairs.

_Thanks, you're so comforting. _

He takes his hand and in a rhythmic motion pats his thigh. I sit down quickly, and continue to watch his movements. He harmonizes to the beat he is putting out for me to hear. I tilt my head in slight confusion, and realize he's about to sing. I stay quiet. I think I'm more nervous now then I was a second ago. In the back of my mind, I'm thinking I'm getting to sing with Damon, and I'm his only audience.

_Ooh, somewhere over the rainbow, way up high  
there's a land that I dreamed of, once in a lullaby._

He motions for me to pick up the beat and sing. So I do, without question.

_Oh, somewhere over the rainbow, skies are blue  
And the dreams that you dare to dream, really do come true._

He smiles and nods and closes his eyes, tapping to the beat now. Then we burst into the bridge together.

_Someday I'll wish upon a star, and wake up where the clouds are far behind me  
Where troubles melt like lemon drops, and high above the chimney tops  
That's where you'll find me  
Oh, somewhere over the rainbow, bluebirds fly.  
Birds fly over the rainbow, why then why, can't I? _

We harmonize, and I feel trapped in his gaze. He's having fun, and my shell is completely cracked. He stands up, "You ready now, Gilbert?" Damon chuckles again.

I roll my eyes as I feel my cheeks blush. "I suppose."

"Good luck, first night, I hope you have your set list," he reminds me in the kindest way possible without scolding me.

I nod, "Yes, Damon, I do." Making my way to the front of the stage, I peek outside of the curtain. It's a packed house tonight. I am terrified and excited in all the same motions.

I breathe in as I'm being introduced. That's my cue.

I grab my guitar, and head out to the stage. The adrenaline is crowding me. I feel it, and the feeling is marvelous. My idea of adding a few more songs was going to be unexpected for me, but here goes nothing.

"Hello, New York!" I greet in the microphone. The crowd cheers, I see my best friends: Bonnie Bennett, Matt Donovan, and Caroline with Klaus by her side.

I start the show with "Angel." It makes the crowd come alive. I have the biggest smile on my face that no one can wipe away at this moment. I proceed with "Bottle it Up;" another song I wrote about Stefan. I'm hoping he's heard it.

I watch the crowd and their emotions. They like me. Me. "Next I'll do a dedication to my favorite city in the world, New York, this one is for you!" I yell. My emotions are wrapped up in this experience. I can't believe I never got to do this. I feel indebted to Damon already. My dedication to New York includes a medley of "Theme from New York, New York," by Frank Sinatra and "New York State of Mind," by Billy Joel.

The next song shocks me. I don't even know how to introduce it, but it appears just like word vomit from my lips. "This is one of my new favorite songs. I gulp, looking behind me to see if Damon was around. I play the beginning of "The Heart of Life."

Suddenly, the crowd emerges with cheers. They know it. I burst into the chorus like it's nothing. It has so much raw feelings; I don't even know where I am. But I know I'm in this song, and I'm trapped. My last few songs include an acapella version of "How Deep is Your Love," and my hit, "Love Song."

"Thank you, New York, it's been my pleasure to play for you." I bow.

My performance of Damon's song is the only thing playing back in my head, what he thinks, what he might say. I gulp and head backstage and I almost bump into a speechless Damon Salvatore.

"H-Hi," I stutter once again.

"Think you blew the roof off," he whispers. I still hear the crowd cheering; I hear Bonnie whistling, and Matt doing the same.

"Oh, that's great," I smile. The smile won't leave my face.

He clears his throat. "Nice song choices."

I nod and remain quiet.

"You have a meet and greet to do," he reminds me. Damon leads me to table full of high resolution photos of me. "There's a cd of your hits and photos, if you they want a signature."

I suddenly get overwhelmed by fans. I'm shocked. I didn't know this many people liked my music. I was blown away, and I think Damon was too, who I occasionally looked up to who was next to me the whole time.

After I finished with my last fan, I was rushed to the back to find my things and leave. I sit in the small dressing room, taking in everything that had happened tonight. I suddenly feel someone staring at me, expecting it was Caroline. I turned my chair around to view in the mirror: Damon.

"You wanna celebrate?" he questioned. He was leaned up against the door frame, in his black boots, along with his leather jacket, and his dark jeans with the grey t-shirt.

"Sure."

I grab my purse, and walk side by side with Damon. It's a weird feeling. I feel the goose bumps creep up my arm as we exit the place. "Your car or mine?" he questions breaking the silence in my head.

"Oh, mine's fine. I probably need to get home soon anyway."

"Then both, I suppose," he changes his mind. I sigh.

I get into my car and so does he. His car is ten times nicer than mine. The slick black Audi parked a few spots away from my old car.

We enter _The Timbers_. Preceding that, we are greeted by my friends. How did he know?

"Hi!" I laugh hugging them all.

"You did great, Lena! I'm so happy for you!" Bonnie says loud enough for everyone to hear.

"Thanks, Bon!" I hug her again.

Damon stands back and watches us. "Nice work, Gilbert!" I hear Matt yell over the sea of people. We make our way to the bar.

_Fuck! _I say in the back of my head. It's karaoke night at The Timbers. I keep forgetting.

Caroline orders rounds for everyone, and we drink.

We drink so much I forget I'm Elena Gilbert, and I giggle while I'm drunk.

After my fifth drink, I'm cackling, and hitting on Damon every chance I get.

"I liked…when you sang my song," he leans over slurring his words all over me. I giggle.

"You're kind of cute when you're drunk," I chuckle.

"Oh I'm cute huh?" he smiles his hardest. It's hard, Damon is forcing it, and Damon is a lunatic when he's drunk.

Caroline and Bonnie are watching us. It's getting awkward, but I don't give a shit.

Oh shit. Taylor Swift comes on. Not the time at all.

We are bonding over "We Are Never Ever Getting Back Together."

The bar is watching us also. Oh crap.

"Like _ever_," Damon slurs with a sarcastic laugh.

"Damon Salvatore, you idiot," I groan in a dramatic voice.

"Love is idiotic," he replies.

He moves closer to me as we are practically touching.

"Not all the time," I answer.

"True."

"Me and Ka-my ex, broke up so many times it should be in a Taylor Swift song," he rolls his eyes.

I know it's Katherine, but does he know that I know? I ponder for a moment.

"Stefan was a douche," I grunt.

He laughs, "Stefan has always been a douche in this music business. What Stefan wants Stefan will always get. I hope him and Katherine are two peas in a pod filled with happiness."

I roll my eyes. "I need to get home…" I didn't want to talk about this, not right now.

"I shouldn't have brought up the past," he mumbled.

I shrugged. _No, you shouldn't have._ "It's fine; I mean gotta get out sometime." I breathed, as I watched him not say a word. "I had a good time," I add. What else could I possibly say? I was speechless around him.

"Me too," he replies.

I'm shocked he feels that way. I didn't know if I amused him or he hated me. I make my way to the exit of the bar and almost trip over my own two feet.

"Ah, has someone never gotten drunk before?" he asks.

I roll my eyes. "And what are you, a pro?"

He chuckles. "When you are in this business, you become one quickly."

"Let me take you home, my driver will make sure we both land on our doorsteps."

I stare at him. "What about my car!?"

"It will be in your driveway when you wake up tomorrow. You have a show tomorrow in New Jersey. Get some sleep okay?" he coaches me even when he is drunk.

I shrug. "Fine, I'll get some sleep." Agreeing seemed like the only good thing to do in my state of mind.

"You did great tonight, Elena. You should be proud."

I nod, leaning my head against the backseat, drowning in my feelings. I feel more word vomit come up. "Are you coming to New Jersey with me?"

"I have to go as your manager, and second, I really wouldn't want to miss it."

I smile softly to myself, as we finally stop at my apartment's doorstep. "Goodnight, Elena."

"Night, Damon."

* * *

**I'd love to hear what you guys want to see, and what you hope for this story. Thank you again. Reviews are lovely xo.**


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